Lithium Hydroxide → 4-[1-({[5-Chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]-benzoic acid

HRID 870036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870036
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH:10]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)[CH3:11])=[O:8])=[C:4]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH:3]=1.[Li+].[OH-]>C1COCC1.CO>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH:10]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=2)[CH3:11])=[O:8])=[C:4]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH:3]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 45140205Methyl 4-[1-({[5-chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]benzoate

Produkt 1

HCID 249525754-[1-({[5-Chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 4-[1-({[5-chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]benzoate from Example 1, Step 10 (81.0 mg, 0.181 mmol) and LiOH (0.9 mL, 1M in water) in THF (1.5 mL) and methanol (1.5 mL) was stirred overnight at r.t. and concentrated. The residue was diluted with 1N HCl and extracted with EtOAc. The organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the desired product as a white solid. MS (−ESI): m/z 432.0 (M−1)−.

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe residue was diluted with 1N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-820e357dc3c4446da24808c47394bb62
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969394B2

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